Synthetic resin and process of making



PatentedJuly 19, 1932 UNITED STATES PATENT OFFICE CHARLES G. MOORE, OF LAKEWOOD, AN'D MILTON ZUCKER, OF CLEVELAND, OHIO, AS-

SIGN'OBS TO THE GLIDDEN' COMPANY, 01 CLEVELAND, OHIO, A. CORPORATION OI OHIO SYNTHETIC RESIN AND PROCESS LIAKING No Drawing.

Synthetic resins have been known in the art for a number of years. Of these, resins of the polyhydric alcohol-polybasic acid type have been known consequent to the investi- 5 gations of J. Watson Smith (Journal Soc. Chem. Ind. 1901: 107 5). Fpr these, generally ghthalic anhydride and glycerol, with a mo ifying acid, are employed. Of such synthetic resins, the various types oifer certain advantages, coupled however with certain disadvantages, andalthough introduced for usalgg' in liquid coating compositions, drawbac ersist. We have found that phthalic acid-g ycerol with modifying acid resins are not satisfactory for spirit varnishes, not having such toughness and elasticity as is desirable, and not being ,sufliciently waterproof.

If high molecular -weight acids, such as the acids of the fatty oils, be employed as the modifying acid, the same difliculties persist.

If tung oil acids be employed, the lack of water resistance is overcome to some extent, but

not a suficiently large percentage can be incorporated, since it is found that the ,tung oil acids tend to produce an insoluble gel on heating. In accordance withour present in- "vention however, a highly flexible waterproof resin can be pre ared by a suitable modification of the polyhydric alcohol-polybasic acid resins.

In its general aspects, the invention contemplates preparing a polyhydric alcoholpolybasic acid type resin such that the entering constituents react in the presence of a soluble-phenolic resin. -If the latter ex-, ceeds 50 per cent. by weight of mixture, the resultant product is not clear, and for use in a spirit varnish gives a spotty, dull film. Below 50 per cent. however, the product is excellent for spirit varnishes, the film obtained from the dissolved resin being clear and glossy. I

For the preparation of the products in accordance with the present improvements, a polyhydric alcohol,as glycerol, polyglycerol, glycol, and the like, together with a olybasic acid, for instance phthalic anhy ride, are brought into reaction along with amodifying monobasic acid, particularly an aliphatic or a fatty'acid, such as'an' unsaturated fatty Application filed June 10, 1829. Serial No. 368,918.

acid of the character derived from dryingoils, and in the presence of the phenolic resin. For the latter, there may be employed any of the soluble condensation products of a phenol and aldehyde or ketone, such phenolic resins or phenol alcohols or soluble phenol-condensation products being readily formed by any of the procedures known, and requiring no precise detail description here.

In the preferred form of our invention, we take cresylic acid (or mixed cresols with posslbly some phenol) and paraldehyde in equimolar proportions, and. heat until reaction takes place and a primary condensation product is formed. 10 parts of this cresolalcohol, after purification to remove excess cresol, are then added to the reaction mixture comprising 45 parts of phthalic anhydride. 22 parts of glycerol, and 23 parts of linseed O11 acids. This reaction mixture is heated at a temperature of about 250 (3., preferably in an inert atmosphere, until a test sample shows the desired degree of toughness. This occurs shortly before a critical point is reached wherein the soluble modification goes over into an insoluble form of the resin. We prefer therefore to cool the resin rapidly either by pouring it out of. the kettle into a container which may be subjected to cold, or by diluting the molten resin with solvent in the manner of preparation of oleoresinous varnish.

If instead of the glycerol, polyglycerol o glycol be employed, or other fatty acids be substituted for the linseed,oilacids,.-corresponding products may be had. For instance, the use of castor oiL "*cids gives a; resin well suited for mixing wit lacquer. Thus, within the scope of the invention, products may be prepared which afi'ord in high degree characteristics adaptable to commercial varnish usage, for tough elastic and waterproof films, and with such further qualities as to miscibility in lacquers, etc., as may be desired.

Other modes of applying the principle of the invention may be employed, change being made as regardsthedetails described, provided the steps or constituents. stated in. any

alcohol, an organic polybasic acid, a monobasic aliphatic acid, and a preformed soluble phenolic resin of the type formed from the group of reactants consisting of aldehydes and ketones.

3. The reaction product of a polyhydric alcohol, an organic polybasic acid, an unsaturated fatty acid, and a preformed soluble phenolic resin of the type formed from the group of reactants consisting of aldehydes and ketones.

4. The reaction product of a polyhydric" alcohol, an organic polybasic acid, a drying oil ftty acid and a preformed soluble phenolic resin of the type formed from the group of reactants consisting of aldehydes and ketones. 1

5. The reaction product of a polyhydric alcohol, an organic polybasic acid, linseed oil acids, and a preformed soluble phenolic resin of the type formed from the group of reactants consisting of aldehydes and ketones.

6. The reaction product of a polyhydric alcohol, an organic polybasic acid, an organic monobasic acid, and a preformed soluble cresylic acid-paraldehyde resin.

7. The reaction product of a polyhydric alcohol, an organic polybasic acid, a monobasic aliphatic acid, and a preformed soluble cresylic acidrparaldehyde resin.

8. The. reaction product of a polyhydric alcohol, an organic polybasic acid, an unsaturated-fatty acid, and a preformed soluble cresylic acid-paraldehyde resin.

9. The reaction product of a polyhydric alcohol, an organic polybasic acid, a drying oil fatty acid, and a preformed soluble cresylic acid-paraldehyde resin. 7

10. The reaction product of a polyhydric alcohol, an organic polybasic acid, linseed oil acids, and a preformed soluble cresylic acidparaldehyde resin.

11. A process of the character described, which comprises reacting between a polyhydric alcohol, an organic polybasic acid, and an organic monobasic acid. in the presence of a preformed soluble phenolic resin of the type formed from the group ofreactants consisting of aldehydes and ketones.

12. A process of the c' racter described, which comprises reacting etween a polyhy-' dric alcohol, an organic polybasic acid, and a monobasic aliphaticacid, in the presence bf apreformed soluble phenolic resin of the dric alcoho 13. A process of the character described,

whichcomprises reacting between a polyhydric alcohol, an organic polybasic acid, and an unsaturated fatty acid, in the presence of a preformed soluble phenolic resin of the type formed from the group of reactants consisting of aldehydes and ketones.

14. A process of the character described, whichcomprises reacting between a polyhydric-alcohol, an organic polybasic acid, and

a-drying'oil fatty acid, in the presence of a preformed soluble phenolic resin of the type formed from the group of reactants consisting of aldehydes and ketones.

15. A process of the character described,

which comprises reacting between a polyhydric alcohol, an'organic polybasic acid, and linseed oil acids, in the presence of a preformed soluble phenolic resin of the type formed from the group of reactants consisting of aldehydes and ketones.

16. A process of the character described, which comprises reacting between a polyhyan organic polybasic acid, and an organic nionobasic acid, in the presence of a preformed soluble cresylic acid-paraldehyderesin.

17 A process of the character described,

dric alcohol, an organic polybasic acid, and a monobasic aliphatic acid, in the presence of a preformed soluble cresylic acid-paraldehyde resin.

- which comprises reacting between a polyhy- '18. A process of the character described,

which comprises reacting between a polyhydric alcohol, an organic polybasic acid, and an unsaturated fatty acid, in the presence of a preformed soluble cresylic acid-paraldehyde resin.

19. A process of the character described, which comprises reacting between a polyhydric alcohol, an organic polybasic acid, and a drying oil fatty acid, in the presence of a preformed soluble cresylic acid-paraldehyde resin.

20. A process of the character described, 

